Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor

Yue Pan, Jian Qiu, Richard B. Silverman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

89 Scopus citations

Abstract

Previously it was found that a conformationally rigid analogue (2) of the epilepsy drug vigabatrin (1) did not inactivate γ-aminobutyric acid aminotransferase (GABA-AT). A cyclic compound with an exocyclic double bond (6) was synthesized and was found to inactivate GABA-AT, but only in the absence of 2-mercaptoethanol. The corresponding difluoro-substituted analogue (14) was synthesized and was shown to be a very potent time-dependent inhibitor, even in the presence of 2-mercaptoethanol.

Original languageEnglish (US)
Pages (from-to)5292-5293
Number of pages2
JournalJournal of Medicinal Chemistry
Volume46
Issue number25
DOIs
StatePublished - Dec 4 2003

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

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